Montegrossi Holiday Rentals, Gaiole in Chianti: Private House Rentals

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Our top choices for Montegrossi hotels

An outdoor dining area with a pool, potted plants, and umbrellas.

A villa with a swimming pool, outdoor seating, and a garden.

A restaurant with a table set for two, overlooking a scenic landscape.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

1. Relais Vignale & Spa

Radda in Chianti

Ali

฿5,831

฿7,575 total

includes taxes & fees

27 Oct - 28 Oct

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A sunlit patio with a glass roof, stone walls, and outdoor seating.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

2. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Michelle

฿11,140

฿12,633 total

includes taxes & fees

30 Oct - 31 Oct

A pool table in a room with curtains, a ceiling with fluorescent lights, and a wall-mounted clock.

A hotel room with a large bed, two armchairs, a small table with a tray of breakfast items, a television, and curtains.

A modern hotel lobby with a curved reception desk, seating area, and a bar.

A spacious lobby with a reception desk, seating area, and a large vase.

3. Hotel Valdarno

Montevarchi

Emmanuel

฿4,023

฿4,425 total

includes taxes & fees

1 Nov - 2 Nov

A spa area with stone walls, a white massage chair, and a potted plant.

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

A narrow street with buildings on either side, a flag, and a bench.

A couple dining at an outdoor table with a view of the countryside.

4. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

฿3,504

฿4,081 total

includes taxes & fees

23 Nov - 24 Nov

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

5. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

฿9,191

฿10,412 total

includes taxes & fees

16 Nov - 17 Nov

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

6. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Ariel

฿3,706

฿4,379 total

includes taxes & fees

27 Oct - 28 Oct

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.

7. Hotel Villa Campomaggio

Radda in Chianti

Dario

฿5,570

฿6,354 total

includes taxes & fees

27 Oct - 28 Oct

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

A dining area with a table and chairs, a view of a landscape through an arched window, and a large umbrella providing shade.

8. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

฿9,077

฿10,212 total

includes taxes & fees

26 Oct - 27 Oct

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A historic stone building with a large arched window and a small balcony.

A stone building with a tower, surrounded by people dining at tables with candles.

A pool area with a stone wall, a wooden bridge, and a castle-like structure in the background.

9. Castello di Tornano Wine Resort

Gaiole in Chianti

Karina

฿5,133

฿5,949 total

includes taxes & fees

26 Oct - 27 Oct

A staircase with a modern design, featuring a combination of stone steps and a carpeted landing.

A modern kitchen with a built-in microwave, sink, and stove. There is a dining area with a table and chairs, and a window with blinds.

A modern reception area with a wooden reception desk, a metal bowl, potted plants, and a seating area with chairs.

A modern bar area with a curved counter, a coffee machine, and a variety of bottles and glasses on shelves.

10. Delta Hotel

Montevarchi

weixing

฿4,332

฿4,766 total

includes taxes & fees

26 Oct - 27 Oct

A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.

A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.

A white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.

A table set with wine glasses and a candle, viewed through a window with string lights.

11. Tenuta CorteDomina

Radda in Chianti

Edgar

฿7,232

฿8,106 total

includes taxes & fees

3 Nov - 4 Nov

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A table set for breakfast with various dishes, drinks, and a newspaper.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

12. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

฿21,786

฿24,342 total

includes taxes & fees

26 Oct - 27 Oct

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

A large building with multiple rooms, surrounded by a field of lavender.

13. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

฿12,397

฿14,015 total

includes taxes & fees

3 Nov - 4 Nov

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

14. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

฿3,203

฿3,826 total

includes taxes & fees

16 Nov - 17 Nov

A courtyard with a fountain, surrounded by neatly trimmed hedges and trees, viewed through an arched doorway.

An outdoor dining table set with breakfast items, a bottle of orange juice, and a view of a tree and landscape.

A stone building with a tiled roof, a staircase leading to an entrance, and a garden area with a table and chairs.

A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.

15. Pieve Aldina - Relais & Châteaux

Radda in Chianti

Paul

฿11,736

฿13,212 total

includes taxes & fees

1 Nov - 2 Nov

A spa area with a stone ceiling, a pool, and two sun loungers.

A buffet area with various fruits and a bar with bottles.

A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.

A courtyard with outdoor seating, stone walls, and a staircase.

16. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

฿3,317

฿3,875 total

includes taxes & fees

15 Nov - 16 Nov

A historic stone building with multiple windows and a courtyard.

A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

A stone building with outdoor seating and a garden with roses.

A pool area with lounge chairs and a service person attending to a guest.

17. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

฿27,679

฿30,825 total

includes taxes & fees

26 Oct - 27 Oct

A covered outdoor seating area with white chairs and tables, overlooking a scenic landscape with mountains and trees.

A long table set for a formal event, with clear chairs and white tablecloths, under a large chandelier and surrounded by greenery.

A poolside area with a swimming pool, lounge chairs, and a grassy lawn.

An aerial view of a villa surrounded by lush greenery and rolling hills.

18. Il Verreno

Ambra

Minna

฿6,742

฿7,567 total

includes taxes & fees

26 Oct - 27 Oct

An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.

An indoor swimming pool with clear glass walls, wooden beams, and large windows.

A historic building with a stone facade, arched entrance, and a wooden balcony.

19. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

฿3,646

฿4,087 total

includes taxes & fees

8 Nov - 9 Nov

A villa with a swimming pool, outdoor seating, and a tennis court.

A pool area with lounge chairs and umbrellas, a stone planter with flowers, and a building with balconies in the background.

A lobby with a stone archway, a reception desk, and a seating area with a sofa and armchairs.

An aerial view of a property with a swimming pool, tennis court, and vineyard.

20. Villa Curina Resort

Castelnuovo Berardenga

Deanna

฿4,939

฿5,584 total

includes taxes & fees

27 Oct - 28 Oct

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Top Montegrossi Hotel Reviews

Hotel Borgo San Luigi

10/10 Excellent

"It was definitely a place we will return too."

Hotel Athena

10/10 Excellent

"Over all a good hotel in a good location, a little dated but clean and breakfast good"

Hotel Chiusarelli

10/10 Excellent

"Perfect in location, cleanliness,staff, amenities.... Wonderful 👍"

NH Siena

10/10 Excellent

"The room isn't cleaned too well. There were some crumbs that were attracting ants. Other than that- no issues"

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Excellent location. Very nice service."

Hotel Minerva

10/10 Excellent

"The check-in staff were very friendly, helpful, and spoke English. The €20 parking in their garage was very nice and convenient, especially when it rained. Nice view from the room."

Il Chiostro del Carmine

8/10 Good

"Breakfast"

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

La Certosa di Pontignano

10/10 Excellent

"Great location amazing place"

More cheap stays in Montegrossi

Cannon d'Oro

Via Montanini 28 Siena SI

฿1,805

฿2,099 total

21 Nov - 22 Nov

includes taxes & fees

7.8/10 Good! (259 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

฿2,562

฿2,932 total

4 Nov - 5 Nov

includes taxes & fees

7.8/10 Good! (453 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

฿2,646

฿3,024 total

2 Nov - 3 Nov

includes taxes & fees

8.8/10 Excellent! (114 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

฿2,969

฿3,379 total

4 Nov - 5 Nov

includes taxes & fees

10/10 Exceptional! (52 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Get rates

Frequently asked questions

Where is the best place to stay in Montegrossi?

Located 9.1 mi (14.6 km) from the heart of Montegrossi, La Certosa di Pontignano is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Hotel Athena and Hotel Executive. See all available top hotels, or vacation rentals in Montegrossi.

What are some of the best holiday rentals that Montegrossi has to offer?

Borgo Argiano: This holiday home rental outside of Montegrossi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library. See all vacation rentals in Montegrossi.

If I need to cancel my hotel reservation in Montegrossi, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Montegrossi.

What are some hotels with pools in Montegrossi?

Castello di Spaltenna- Small Luxury Hotels of the World: Offers an indoor pool, an outdoor pool and 2 restaurants. Hotel Borgo di Cortefreda Relais and Four Points by Sheraton Siena are two additional hotels that feature an on-site pool. View all hotels with pools in Montegrossi.

How is it to stay in Montegrossi?

Visitors to Montegrossi will definitely find plenty to explore and enjoy. In Montegrossi, there are 4 hotels and other accommodation options to choose from. Find out more about Montegrossi.

What are the top places to visit in Montegrossi?

Places to visit in the wider area include Badia a Coltibuono, Meleto Castle and Cantalici Winery. You'll also find Castello di Albola and Castello di Radda Winery in the area. Take a look at what more there is to see and do in Expedia's Montegrossi guide.

What's the seasonal weather like in Montegrossi?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Montegrossi is 946 mm.

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Book Hotels in Montegrossi on Expedia.it

Find hotels in Montegrossi from ฿2,099

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montegrossi

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Montegrossi hotels

1. Relais Vignale & Spa

2. Castello di Spaltenna- Small Luxury Hotels of the World

3. Hotel Valdarno

4. Palazzo Leopoldo Dimora Storica & Spa

5. Dievole Wine Resort

6. Ultimo Mulino Wellness Country Hotel

7. Hotel Villa Campomaggio

8. Chapter Chianti, a Member of Design Hotels

9. Castello di Tornano Wine Resort

10. Delta Hotel

11. Tenuta CorteDomina

12. Hotel Le Fontanelle

13. Borgo Scopeto Wine & Country Relais

14. La Certosa di Pontignano - Place of Charme

15. Pieve Aldina - Relais & Châteaux

16. Hotel Palazzo San niccolò & Spa

17. Borgo San Felice Resort

18. Il Verreno

19. Villa Casagrande Resort & SPA

20. Villa Curina Resort

Top Montegrossi Hotel Reviews

Hotel Borgo San Luigi

Hotel Athena

Hotel Chiusarelli

NH Siena

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Minerva

Il Chiostro del Carmine

Hotel Italia

La Certosa di Pontignano

More cheap stays in Montegrossi

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Torre del Fuggisole

Porta Pispini Residence

Villa Norcenni Aparthotel

Frequently asked questions

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